Sulfuric Acid → (1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester

HRID 250301

反応式

HRID 250301 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)CCC>[CH2:4]([O:14][C:13](=[O:15])[CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1])[CH2:5][CH2:6][CH3:7]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 20825N-PhthaloylglycineHCID 516892Sodium Bicarbonate

生成物 1

HCID 357739(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester収率 194.4%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A mixture of 160 ml of butanol, 20.0 g of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid (94.6 mmol) and 2.0 ml of concentrated sulfuric acid was refluxed with stirring for 24 h. Then 5 g of sodium bicarbonate were added in portions, stirring continued at r.t. for 5 min and the solvent evaporated in vacuo. The residue was partitioned between 100 ml of water and 100 ml of ethyl acetate. The organic phase was washed with 100 ml of brine, dried over sodium sulfate and was evaporated in vacuo to give a yellowish oil that later solidified. 24.02 g of the title compound were obtained; MS-(+)-ion: M+1=261.9 amu.

後処理

  1. temperaturewas refluxed
  2. stirringstirring
  3. waitcontinued at r.t. for 5 min
  4. customthe solvent evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of water and 100 ml of ethyl acetate
  6. washThe organic phase was washed with 100 ml of brine
  7. dry with materialdried over sodium sulfate
  8. customwas evaporated in vacuo
  9. customto give a yellowish oil that

出典と根拠

ORDレコード
ord-72c187b5bf18473fbcce2d7f51e3acef
出典データセット
uspto-grants-2011_01
特許番号
US07863292B2

関連ノート

読み込み中…